Nitrogen management is vital for economic and environmental sustainability. Asynchrony of fertilizer application with crop demand along various nitrogen losses in Eastern India leads to low fertilizer efficiency in Kharif rice. At the same time, direct-sowing is gaining popularity due to water and labor scarcity. In an experiment between 2017–2018 in West Bengal, India, the main plots represented establishment methods: conventional transplanting, TPR; direct-seeded rice, DSR; and drum seeded rice, DRR; while subplots represented nitrogen management options: farmer’s practice (FP), the state-recommended (SR), nutrient expert-based (NE), Green seeker-based (GS) and LCC-based (LCC) in a split-plot design with three repetitions. Plant growth, productivity, and profitability were evaluated. All indicators of growth or production were affected by establishment methods and by N-management options. The yield enhancement of TPR and DSR over DRR was 21.1 and 16.8%, respectively, while it was enhanced by 19.21, 14.71, 6.49, and 2.52% by GS, NE, LCC, and SR, respectively, over FP. The highest net return and return per rupee invested were recorded with DSR, while both GS and NE had better economics. The results suggest that the combination of DSR establishment with GS or NE requires further studies to find climate-smart management techniques in Kharif rice.